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Leadership Manifesto Part 2 To be a true leader, you need to communicate

Effective communication starts with active listening. Modern American conversation patterns often have people formulating their response or next statement while the other party is talking.

Leadership Manifesto Part 2 To be a true leader, you need to communicate


Humans, and by extension businesses, are not rational. Human relationships are about feeling safe. That is why communication and empathy are critical to a leader’s success.


Effective communication starts with active listening. Modern American conversation patterns often have people formulating their response or next statement while the other party is talking. This gives the perception that conversation is moving quickly and minimizes the “downtime” in a conversation to give us control over the conversation. Listening, true listening with the genuine intent to understand, is the key to controlling a conversation and driving to a successful outcome. When you listen, you come to know twice as much as the other party in the conversation; you know what you already know, plus you know what the other person knows as well.


Human beings put a premium on time, whether subconsciously or consciously because it is an equal and non-redeemable commodity. For instance, if you spend money, you can make more money, but if you spend time, you’ll never get it back. Because of this, a leader’s time is one of the most essential relational tools in your inventory. However, leaders are often getting pulled in a dozen different directions at once, which makes the time expenditure of the leader in an intentional and focused manner all the more significant.

When thinking about communication, there are two extreme ends of the spectrum: Rational and Emotional.

Emotional Spectrum Whiteboard
Credit: Tim Gast, based on the works of Simon Sinek

Rational communication tends to be transactional and driven by logic. An example of rational communication would be: “If X is true, then Y is also true, and therefore Z is false.” Most business communication tends to take place near the rational end of the spectrum. At this end of the spectrum, communication is much more analytical, and personal empathy is low.

Emotional communication is the far opposite end of the spectrum. This type of communication is not driven by logic but by emotions, feelings, and perceptions. In times of crisis, emotions rise, and people naturally swing towards the emotional end of the spectrum. When operating on this end of the spectrum, listening and empathy are crucial.

Emotional Intelligence

The capacity to be aware of, control, and express one's emotions and handle interpersonal relationships judiciously and empathetically.

As a leader, you need to be introspective and aware of where you are on the emotional spectrum. You must exercise emotional intelligence to know where other parties are on the emotional spectrum and engage them appropriately. Often we have the perception that when engaging with highly emotional people, you should take as much emotion out of the interaction as possible, when in fact, the opposite is true. If you take emotion out of your responses, that causes you to appear cold and uninterested, further escalating the other person. When you are engaged in a highly emotional interaction, you should mirror some of that emotion, albeit at a slightly lower level, to cause a natural de-escalation of the situation.

When mirroring emotion, it is critical that you don’t direct it back at the other person; that will cause a fight and escalate tensions.

Practically, when working with others in your organization, you should continue the continuum of rationality in parallel with the emotional spectrum when communicating.

Continuum of Rationality Whiteboard
Credit: Tim Gast, based on the works of Simon Sinek

Example: An email is a rational tool. Don’t answer emotional questions through rational tools. Pick up the phone, jump on a VC, or walk over if possible and speak in person.

Regardless of the tool used, effective and direct communication must be

  • Clear — the intent of your message needs to be clear and easily understood.
  • Concise — use the minimum words necessary for a clear message.
  • Accurate — leaders must maintain ultimate integrity.
  • Confident — the message should be strong. The leader must be communicating from a place of belief in the message.

Leading up and down the chain of command

One of the most important jobs of any leader is to support your boss. Leadership must always present a united front to the employees. A public display of discontent or disagreement with the chain of command undermines the authority of leaders at all levels. This is catastrophic to the performance of any organization.

As a leader, if you don’t understand why decisions are being made, requests denied, or support allocated elsewhere, you must ask those questions up the chain. Then, once understood, you can pass that understanding down to your team. Leaders in any chain of command will not always agree. But at the end of the day, once the debate on a particular course of action is over and the boss has made a decision — even if that decision is one you argued against — you must execute the plan as if it were your own.

The major factors to be aware of when leading up and down the chain of command are these:

  • Take responsibility for leading everyone in your world, subordinates and superiors alike.
  • If someone isn’t doing what you want or need them to do, look in the mirror first and determine what you can do to enable this better.
  • Don’t ask your leader what you should do: tell them what you are going to do.

How do you win with people you don't like?

When you lead within an organization, you will inevitably have to work with people you simply don’t like. It is crucial to building (productive) relationships with people so that you can have more influence across your team, organization, and company.

There are a couple of practical things to keep in mind when you’re interacting with people you don’t like

  • Don’t be a jerk; you’ll make things worse.
  • Don’t undermine; carry yourself with humility. Try and build a relationship instead of being antagonistic.
  • Most of the time, when you “don’t like” someone, it’s because your ego is getting in the way.
    • To quickly check your ego, ask yourself, “If I am so smart, why am I not winning?” If you are answering that question honestly, you will put your ego in check.
    • Ask yourself, “Is this going to help the relationship or hurt it?”

What about dealing with people that lack common sense?

Common sense is the blanket term we use that covers a person’s natural ability to make good decisions.

To help improve someone’s decision making, you need to teach them how to

  • Step back and detach. You cannot understand a complex and dynamic landscape when you are deep in the weeds and focusing on the ground level.
  • Analyze and determine courses of action and understand the consequences of action (including second and third-order effects). Nobody wants to make bad decisions on purpose. However, when poor decision-making is observed, it usually stems from a reasonable decision being made on the ground without understanding or considering the downstream effects.
  • Mitigate risk. Understand your assets and resources and where they can be applied to minimize the threat surface and unintended downstream effects.

Good decision-making isn’t something that can be learned through reading or observation alone. It is developed through doing. Therefore, if you have someone that doesn’t seem to exhibit a lot of common sense, the best thing you can do is to put them in charge of something that is just outside of their competency. As you give these people a little bit of space to make decisions, you need to gently correct their mistakes and help them understand the decision-making process rather than smacking them for making a wrong decision.

Some behavioral patterns of a leader

  • The phrase “not my job” doesn’t exist in our vocabulary.
  • We individually accept responsibility for outcomes, both successful and unsuccessful.
  • When things go wrong, the only place we look to point the finger is at ourselves, individually.


There is no such thing as perfection. It’s a lesson all elite organizations understand. Perfect execution cannot be achieved. Instead of searching for it, they define perfection as finding and fixing every mistake. Perfection is setting your ego aside and explaining to your team what you did wrong. Perfection is building a culture where your team is willing to expose every error, even those that could be hidden or ignored. Perfection is creating a team that competes over whose fault it is when a project fails or when goals aren’t reached.

It’s time to redefine perfection. Perfection is about mistakes. You must teach your mistakes to others, so they learn them in the classroom, the boardroom, and the debrief. You must teach your mistakes to others, so they don’t make them in combat, on a sales call, during a negotiation, or when fighting a fire, running a business, or leading a team.

Sources and Resources

Much of the content of this document has been borrowed from these resources:

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Effective communication starts with active listening. Modern American conversation patterns often have people formulating their response or next statement while the other party is talking.